If both players have chosen, say, William Coxwish to lead their troop in a 250 points game, doesn't it result in a very lopsided battle in favour of whoever happens to win the bid and gets William? I mean, yes, they are down some Maravedies but the other guy is down a 75-point leader. How has your experience been?

Till now I have never seen that, because usually people ask the opponent what is he gonna use, but you're right. Loosing a bidding is the beginning of the end XD It's a way to control the use of Personalities.